CH428738A - Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden - Google Patents

Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Info

Publication number: CH428738A
Authority: CH; Switzerland
Prior art keywords: hexamethylene; benzenesulfonyl; semicarbazide; acid; methyl
Prior art date: 1961-09-09

Application number

CH1065762A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Muth Karl

Weber Helmut

Haack Erich

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1961-09-09

Filing date

1962-09-07

Publication date

1967-01-31

1962-09-07 Application filed by Hoechst Ag filed Critical Hoechst Ag

1967-01-31 Publication of CH428738A publication Critical patent/CH428738A/de

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 5
LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title description 3
239000002253 acid Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000009825 accumulation Methods 0.000 claims 1
-1 alkyl radical Chemical class 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 7
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000008331 benzenesulfonamides Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
239000000155 melt Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MUBJNMWVQGHHLG-UHFFFAOYSA-N 3-bromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(Br)=C1 MUBJNMWVQGHHLG-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
KQRMGBSYWRUESQ-UHFFFAOYSA-N (2-chlorophenyl)sulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1Cl KQRMGBSYWRUESQ-UHFFFAOYSA-N 0.000 description 1
QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical compound NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
IDAXFFOLDRMEAO-UHFFFAOYSA-N 3-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC(S(N)(=O)=O)=C1 IDAXFFOLDRMEAO-UHFFFAOYSA-N 0.000 description 1
CRINBBOGNYCAOV-UHFFFAOYSA-N 3-fluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(F)=C1 CRINBBOGNYCAOV-UHFFFAOYSA-N 0.000 description 1
NRPHEJYDQNWSJF-UHFFFAOYSA-N 3-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)N=C=O)=C1 NRPHEJYDQNWSJF-UHFFFAOYSA-N 0.000 description 1
NVZINPVISUVPHW-UHFFFAOYSA-N 3-methylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1 NVZINPVISUVPHW-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
MXWBOVVYTCHHJB-UHFFFAOYSA-N CC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC(C)=O Chemical compound CC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC(C)=O MXWBOVVYTCHHJB-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000243251 Hydra Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
WKIGMCZMEANWKE-UHFFFAOYSA-N methyl N-(3-chlorophenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC(=CC=C1)Cl)=O WKIGMCZMEANWKE-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1065762A 1961-09-09 1962-09-07 Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden CH428738A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF34893A DE1204676B (de)	1961-09-09	1961-09-09	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Publications (1)

Publication Number	Publication Date
CH428738A true CH428738A (de)	1967-01-31

Family

ID=7095767

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1800366A CH438324A (de)	1961-09-09	1962-09-07	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH1065762A CH428738A (de)	1961-09-09	1962-09-07	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH1800266A CH438323A (de)	1961-09-09	1962-09-07	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH1800366A CH438324A (de)	1961-09-09	1962-09-07	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1800266A CH438323A (de)	1961-09-09	1962-09-07	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Country Status (4)

Country	Link
CH (3)	CH438324A (da)
DE (1)	DE1204676B (da)
DK (1)	DK103997C (da)
GB (1)	GB953779A (da)

1961
- 1961-09-09 DE DEF34893A patent/DE1204676B/de active Pending
1962
- 1962-09-07 CH CH1800366A patent/CH438324A/de unknown
- 1962-09-07 CH CH1065762A patent/CH428738A/de unknown
- 1962-09-07 DK DK367163A patent/DK103997C/da active
- 1962-09-07 CH CH1800266A patent/CH438323A/de unknown
- 1962-09-07 GB GB3441062A patent/GB953779A/en not_active Expired

Also Published As

Publication number	Publication date
CH438323A (de)	1967-06-30
DK103997C (da)	1966-03-21
CH438324A (de)	1967-06-30
GB953779A (en)	1964-04-02
DE1204676B (de)	1965-11-11

Publication	Publication Date	Title
DE2524277C2 (da)	1988-08-04
DE2362754C2 (de)	1985-11-21	Cyclopropylalkylaminoreste enthaltende Oxazolinverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
CH628887A5 (de)	1982-03-31	Verfahren zur herstellung von benzolsulfonylharnstoffen.
DE1543564A1 (de)	1970-09-17	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
DE3879378T2 (de)	1993-06-24	Amid-verbindungen.
CH428738A (de)	1967-01-31	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
DE1181208B (de)	1964-11-12	Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen
AT238216B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE2720926A1 (de)	1978-11-23	Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung
DE1937759A1 (de)	1970-09-24	Benzolsulfonylsemicarbazide und Verfahren zu ihrer Herstellung
AT235845B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT236400B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT236402B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE2122070A1 (de)	1972-06-08	1 Veratryl 4 methyl 5 athyl 7,8 dimethoxy 2,3 diazabicyclo eckige Klam mer auf 5,4,0 eckige Klammer zu undeca pentaen (1,3,6,8,10) und seine Verwendung
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT234109B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT236397B (de)	1964-10-26	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
AT236404B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
CH374984A (de)	1964-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE1443908C3 (de)	1974-07-04	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
DE1793111C3 (de)	1976-07-01	Acylaminoäthylbenzolsulfonyl-delta hoch 2-cyclohexenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH427794A (de)	1967-01-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT238215B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT228797B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen